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Hoffmann, R. A wiki for the life sciences where authorship matters. Nature Genetics (2008)

Conformational effects on optical rotation. 2-Substituted butanes.

The specific rotations of 2-substituted butanes (X = F, Cl, CN, and HCC) were calculated at the B3LYP/aug-cc-pVDZ level as a function of the C-C-C-C torsion angle. The results for the four compounds are remarkably similar, despite large differences in the electronic transition energies. The temperature dependence of the specific rotations for 2-methylbutyronitrile and for 2-chlorobutane was studied to give experimental information about the effect of the torsion angle on the specific rotation. The results were in good accord with B3LYP/aug-cc-pVDZ calculations. The specific rotations derived from the study of 2-chlorobutane are similar to those previously obtained for 3-chloro-1-butene, indicating that the double bond does not have a large effect on the optical rotations, but it did lead to a large difference between calculated and observed specific rotations.[1]


  1. Conformational effects on optical rotation. 2-Substituted butanes. Wiberg, K.B., Wang, Y.G., Vaccaro, P.H., Cheeseman, J.R., Luderer, M.R. The journal of physical chemistry. A, Molecules, spectroscopy, kinetics, environment & general theory. (2005) [Pubmed]
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